AR128586A1 - IL-17A MODULATORS BASED ON DI-CYCLOPROPYLE AND THEIR USES - Google Patents

IL-17A MODULATORS BASED ON DI-CYCLOPROPYLE AND THEIR USES

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Publication number
AR128586A1
AR128586A1 ARP230100420A ARP230100420A AR128586A1 AR 128586 A1 AR128586 A1 AR 128586A1 AR P230100420 A ARP230100420 A AR P230100420A AR P230100420 A ARP230100420 A AR P230100420A AR 128586 A1 AR128586 A1 AR 128586A1
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Argentina
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halogen
independently selected
substituents independently
optionally substituted
alkyl
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ARP230100420A
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Spanish (es)
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Paul R Fatheree
Timothy J Church
Martin S Linsell
Margot G Paulick
Maureen Reilly
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Dice Alpha Inc
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Publication of AR128586A1 publication Critical patent/AR128586A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/08—1,2,5-Oxadiazoles; Hydrogenated 1,2,5-oxadiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/08—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/10—Spiro-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pain & Pain Management (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Rheumatology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La divulgación del presente documento proporciona compuestos y composiciones farmacéuticas de fórmula (1) y fórmula (1-A) para la modulación de IL-17A. Los compuestos y las composiciones farmacéuticas de fórmula (1) y fórmula (1-A) son útiles para el tratamiento de afecciones inflamatorias, como la psoriasis. Reivindicación 1: Un compuesto representado por la estructura de fórmula (1), o una sal farmacéuticamente aceptable de este, caracterizado porque: A se selecciona de un carbociclo C₃₋₆ y heterociclo de 5 a 6 miembros, uno cualquiera de los cuales se sustituye opcionalmente con uno o más sustituyentes independientemente seleccionados de (a), (b) y (c): (a) halógeno, -OR¹¹, -N(R¹¹)₂, -C(O)R¹¹, -C(O)OR¹¹, -NO₂ y -CN; (b) alquilo C₁₋₆ opcionalmente sustituido con uno o más sustituyentes independientemente seleccionados de: halógeno, -OR¹¹, -N(R¹¹)₂, -C(O)R¹¹, -C(O)OR¹¹, -NO₂, -CN, carbociclo C₃₋₆ y heterociclo de 3 a 6 miembros, donde cada carbociclo C₃₋₆ y heterociclo de 3 a 6 miembros se sustituye opcionalmente con uno o más sustituyentes independientemente seleccionados de halógeno, -OR¹¹, -N(R¹¹)₂, -C(O)R¹¹, -C(O)OR¹¹, -NO₂ y -CN; y (c) carbociclo C₃₋₆ opcionalmente sustituido con uno o más sustituyentes independientemente seleccionados de halógeno, alquilo C₁₋₄, haloalquilo C₁₋₄, -OR¹¹, -N(R¹¹)₂, -C(O)R¹¹, -C(O)OR¹¹, -NO₂ y -CN; R¹ se selecciona de hidrógeno, halógeno, -OR¹², -N(R¹²)₂, -C(O)R¹², -C(O)OR¹², -NO₂, -CN y alquilo C₁₋₆ opcionalmente sustituidos con uno o más sustituyentes independientemente seleccionados de halógeno, -OR¹², -N(R¹²)₂, -C(O)R¹², -C(O)OR¹², -NO₂ y -CN; R² se selecciona de -N(RA)C(O)(RB) y -N(RC)C(O)N(RD)(RE); el resto de fórmula (2) se selecciona de un heterociclo de 4 a 12 miembros opcionalmente sustituidos con uno o más sustituyentes independientemente seleccionados de: halógeno, -OR¹³, -N(R¹³)₂, -C(O)R¹³, -C(O)OR¹³, -NO₂, -CN y alquilo C₁₋₆ opcionalmente sustituidos con uno o más sustituyentes independientemente seleccionados de halógeno, -OR¹³, -N(R¹³)₂, -C(O)R¹³, -C(O)OR¹³, -NO₂ y -CN; R³ se selecciona de halógeno, -OR¹⁴, -N(R¹⁴)₂, -C(O)R¹⁴, -C(O)OR¹⁴, -NO₂, -CN, alquilo C₁₋₆ y carbociclo C₃₋₆, donde cada alquilo C₁₋₆ y carbociclo C₃₋₆ de los cuales se sustituye opcionalmente con uno o más sustituyentes independientemente seleccionados de halógeno, -OR¹⁴, -N(R¹⁴)₂, -C(O)R¹⁴, -C(O)OR¹⁴, -NO₂ y -CN; RA se selecciona de hidrógeno y alquilo C₁₋₆ opcionalmente sustituidos con uno o más sustituyentes independientemente seleccionados de halógeno, -OR¹⁵, -N(R¹⁵)₂, -C(O)R¹⁵, -C(O)OR¹⁵, -NO₂ y -CN; RB se selecciona de: alquilo C₁₋₆ opcionalmente sustituido con uno o más sustituyentes independientemente seleccionados de: halógeno, -OR¹⁶, -N(R¹⁶)₂, -C(O)R¹⁶, -C(O)OR¹⁶, -N(R¹⁶)C(O)OR¹⁶, -NO₂, -CN; carbociclo C₃₋₆ y heterociclo de 5 a 6 miembros, cualquiera de los cuales está opcionalmente sustituido con uno o más sustituyentes independientemente seleccionados de halógeno -OR¹⁶, -N(R¹⁶)₂, -C(O)R¹⁶, -C(O)OR¹⁶, -NO₂ y -CN; y carbociclo C₃₋₆ y heterociclo de 4 a 6 miembros, cada uno de los cuales se sustituye opcionalmente con uno o más sustituyentes independientemente seleccionados de: halógeno, -OR¹³, -N(R¹⁶)₂, -C(O)R¹⁶, -C(O)OR¹⁶, -NO₂, -CN y alquilo C₁₋₆ opcionalmente sustituidos con uno o más sustituyentes independientemente seleccionados de halógeno, -OR¹⁶, -N(R¹⁶)₂, -C(O)R¹⁶, -C(O)OR¹⁶, -NO₂ y -CN; RC se selecciona independientemente de hidrógeno y alquilo C₁₋₆ opcionalmente sustituidos con uno o más sustituyentes independientemente seleccionados de: halógeno, -OR¹⁷, -N(R¹⁷)₂, -C(O)R¹⁷, -C(O)OR¹⁷, -NO₂ y -CN; RD se selecciona de alquilo C₁₋₆ y carbociclo C₃₋₆, cualquiera de los cuales se sustituye opcionalmente con uno o más sustituyentes independientemente seleccionados de: halógeno, -OR¹⁸, -N(R¹⁸)₂, -C(O)R¹⁸, -C(O)OR¹⁸, -NO₂ y -CN; RE se selecciona de hidrógeno, alquilo C₁₋₆ y carbociclo C₃₋₆, cualquiera de los cuales se sustituye opcionalmente con uno o más sustituyentes independientemente seleccionados de: halógeno, -OR¹⁹, -N(R¹⁹)₂, -C(O)R¹⁹, -C(O)OR¹⁹, -NO₂ y -CN; R¹¹, R¹², R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, y R¹⁹ se seleccionan cada uno independientemente en cada aparición de: hidrógeno; alquilo C₁₋₆ opcionalmente sustituido con uno o más sustituyentes independientemente seleccionados de halógeno, -O-alquilo C₁₋₆, -O-haloalquilo C₁₋₆, -NH₂, -NO₂, =O, -CN, carbociclo C₃₋₁₀ y heterociclo de 3 a 10 miembros, donde cada carbociclo C₃₋₁₀ y heterociclo de 3 a 10 miembros se sustituyen opcionalmente con uno o más sustituyentes independientemente seleccionados de: halógeno, -OH, -O-alquilo C₁₋₆, -O-haloalquilo C₁₋₆, -NH₂, -NO₂, =O y -CN; y carbociclo C₃₋₁₀ y heterociclo de 3 a 10 miembros opcionalmente sustituidos con uno o más sustituyentes independientemente seleccionados de: halógeno, -OH, -O-alquilo C₁₋₆, -O-haloalquilo C₁₋₆, -NH₂, -NO₂, =O y -CN; y n se selecciona de 0, 1, 2, 3 y 4.The disclosure herein provides compounds and pharmaceutical compositions of formula (1) and formula (1-A) for the modulation of IL-17A. The compounds and pharmaceutical compositions of formula (1) and formula (1-A) are useful for the treatment of inflammatory conditions, such as psoriasis. Claim 1: A compound represented by the structure of formula (1), or a pharmaceutically acceptable salt thereof, characterized in that: A is selected from a C₃₋₆ carbocycle and 5- to 6-membered heterocycle, any one of which is substituted optionally with one or more substituents independently selected from (a), (b) and (c): (a) halogen, -OR¹¹, -N(R¹¹)₂, -C(O)R¹¹, -C(O)OR¹¹, -NO₂ and -CN; (b) C₁₋₆ alkyl optionally substituted with one or more substituents independently selected from: halogen, -OR¹¹, -N(R¹¹)₂, -C(O)R¹¹, -C(O)OR¹¹, -NO₂, -CN, C₃₋₆ carbocycle and 3- to 6-membered heterocycle, wherein each C₃₋₆ carbocycle and 3- to 6-membered heterocycle is optionally substituted with one or more substituents independently selected from halogen, -OR¹¹, -N(R¹¹)₂, -C (O)R¹¹, -C(O)OR¹¹, -NO₂ and -CN; and (c) C₃₋₆ carbocycle optionally substituted with one or more substituents independently selected from halogen, C₁₋₄ alkyl, C₁₋₄ haloalkyl, -OR¹¹, -N(R¹¹)₂, -C(O)R¹¹, -C( O)OR¹¹, -NO₂ and -CN; R¹ is selected from hydrogen, halogen, -OR¹², -N(R¹²)₂, -C(O)R¹², -C(O)OR¹², -NO₂, -CN and C₁₋₆ alkyl optionally substituted with one or more substituents independently selected from halogen, -OR¹², -N(R¹²)₂, -C(O)R¹², -C(O)OR¹², -NO₂ and -CN; R² is selected from -N(RA)C(O)(RB) and -N(RC)C(O)N(RD)(RE); the remainder of formula (2) is selected from a 4 to 12 membered heterocycle optionally substituted with one or more substituents independently selected from: halogen, -OR¹³, -N(R¹³)₂, -C(O)R¹³, -C( O)OR¹³, -NO₂, -CN and C₁₋₆ alkyl optionally substituted with one or more substituents independently selected from halogen, -OR¹³, -N(R¹³)₂, -C(O)R¹³, -C(O)OR¹³, -NO₂ and -CN; R³ is selected from halogen, -OR¹⁴, -N(R¹⁴)₂, -C(O)R¹⁴, -C(O)OR¹⁴, -NO₂, -CN, C₁₋₆ alkyl and C₃₋₆ carbocycle, where each C₁ alkyl ₋₆ and C₃₋₆ carbocycle of which is optionally substituted with one or more substituents independently selected from halogen, -OR¹⁴, -N(R¹⁴)₂, -C(O)R¹⁴, -C(O)OR¹⁴, -NO₂ and -CN; RA is selected from hydrogen and C₁₋₆ alkyl optionally substituted with one or more substituents independently selected from halogen, -OR¹⁵, -N(R¹⁵)₂, -C(O)R¹⁵, -C(O)OR¹⁵, -NO₂ and - CN; RB is selected from: C₁₋₆ alkyl optionally substituted with one or more substituents independently selected from: halogen, -OR¹⁶, -N(R¹⁶)₂, -C(O)R¹⁶, -C(O)OR¹⁶, -N(R¹⁶ )C(O)OR¹⁶, -NO₂, -CN; C₃₋₆ carbocycle and 5- to 6-membered heterocycle, any of which is optionally substituted with one or more substituents independently selected from halogen -OR¹⁶, -N(R¹⁶)₂, -C(O)R¹⁶, -C(O) OR¹⁶, -NO₂ and -CN; and C₃₋₆ carbocycle and 4- to 6-membered heterocycle, each of which is optionally substituted with one or more substituents independently selected from: halogen, -OR¹³, -N(R¹⁶)₂, -C(O)R¹⁶, - C(O)OR¹⁶, -NO₂, -CN and C₁₋₆ alkyl optionally substituted with one or more substituents independently selected from halogen, -OR¹⁶, -N(R¹⁶)₂, -C(O)R¹⁶, -C(O) OR¹⁶, -NO₂ and -CN; RC is independently selected from hydrogen and C₁₋₆ alkyl optionally substituted with one or more substituents independently selected from: halogen, -OR¹⁷, -N(R¹⁷)₂, -C(O)R¹⁷, -C(O)OR¹⁷, -NO₂ and -CN; RD is selected from C₁₋₆ alkyl and C₃₋₆ carbocycle, either of which is optionally substituted with one or more substituents independently selected from: halogen, -OR¹⁸, -N(R¹⁸)₂, -C(O)R¹⁸, - C(O)OR¹⁸, -NO₂ and -CN; RE is selected from hydrogen, C₁₋₆ alkyl and C₃₋₆ carbocycle, any of which is optionally substituted with one or more substituents independently selected from: halogen, -OR¹⁹, -N(R¹⁹)₂, -C(O)R¹⁹ , -C(O)OR¹⁹, -NO₂ and -CN; R¹¹, R¹², R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, and R¹⁹ are each independently selected at each occurrence of: hydrogen; C₁₋₆ alkyl optionally substituted with one or more substituents independently selected from halogen, -O-C₁₋₆ alkyl, -O-haloC₁₋₆ alkyl, -NH₂, -NO₂, =O, -CN, C₃₋₁₀ carbocycle and heterocycle 3 to 10 membered, wherein each C₃₋₁₀ carbocycle and 3 to 10 membered heterocycle are optionally substituted with one or more substituents independently selected from: halogen, -OH, -O-C₁₋₆ alkyl, -O-C₁₋haloalkyl ₆, -NH₂, -NO₂, =O and -CN; and C₃₋₁₀ carbocycle and 3 to 10 membered heterocycle optionally substituted with one or more substituents independently selected from: halogen, -OH, -O-C₁₋₆ alkyl, -O-C₁₋₆ haloalkyl, -NH₂, -NO₂, =O and -CN; and n is selected from 0, 1, 2, 3 and 4.

ARP230100420A 2022-02-25 2023-02-23 IL-17A MODULATORS BASED ON DI-CYCLOPROPYLE AND THEIR USES AR128586A1 (en)

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KR100477070B1 (en) 1994-03-25 2006-04-21 이소테크니카 인코포레이티드 Enhancing the efficacy of pharmaceuticals by deuteration
US6334997B1 (en) 1994-03-25 2002-01-01 Isotechnika, Inc. Method of using deuterated calcium channel blockers
US11447468B2 (en) * 2019-02-06 2022-09-20 Dice Alpha, Inc. IL-17 ligands and uses thereof
MX2022003166A (en) * 2019-09-16 2022-06-29 Dice Alpha Inc Il-17a modulators and uses thereof.

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